16-year-old Nick Twisp (Michael Cera) is in his bedroom masturbating. Nick is a smart mouthed, Sinatra-loving, introspective teen who feels depressed about the fact that he is still a virgin. He goes downstairs to have breakfast with his mother, Estelle (Jean Smart), and her new boyfriend, Jerry (Zach Galifianakis). Jerry is a sleaze ball and he and Nick have a strained relationship. Estelle and Nick’s father, George (Steve Buscemi), are divorced and Estelle relies on George’s child support payments to stay afloat. Nick’s neighbor, Judd Ferguson (Fred Willard)  a harborer of illegal immigrants and inciter of public riots  stops by to give Nick the mail from Nick’s mailbox. Nick describes his fondness for Mr. Ferguson but notes that he is a bit weird.

Nick spends time with his best friend Lefty (named after his slanted penis) talking about girls and Lefty’s unrequited love for Millie Filbert. When he goes back home, he finds three Marines outside his door looking for Jerry. Jerry sold them a car which gave out after 50 miles (and had a banana in the engine) and the Marines want their $900 back. Nick tells them that Jerry spent their money and that they should come back later. The Marines leave the car behind and spray paint a death threat for Jerry on it. Jerry sees that the Marines mean business, so he decides to take Estelle and Nick camping to get away from the trouble.

The trio stays in an old run down trailer Jerry’s friend lent him in a trailer park in Ukiah. Nick is unhappy about the conditions and asks his mom how much longer Jerry will be around. Estelle makes it clear that she doesn’t have high hopes for her prospects since she is 49, has stretch marks and no income. She goes into the “master bedroom” to have sex with Jerry. Nick is left dejectedly staring at the dishes.

The next morning, Nick goes to take a shower in the trailer parks showering area. On his way there, he crosses paths with Sheeni Saunders (Portia Doubleday). She jokes that his robe is open and walks into the women’s shower. Nick is shown in the shower, smitten. When Nick goes back to his trailer, he finds Sheeni talking to Estelle. Estelle tells Nick to go and help Sheeni carry her groceries to her trailer.

The pair goes shopping and Sheeni brings Nick to her house. She tells him that her parents are very religious and at church, so she offers to give him a tour of her obscenely large, two-floored trailer. She shows him her room and the two talk about foreign films and various musicians. Nick is head over heels but awkward around her. As she walks him out, he gets the nerve to ask her to the beach.

The next day, Nick goes to collect Sheeni. He meets her father, a former lawyer, who tells Nick that by taking Sheeni out, he has entered a verbal contract to look after her and ensure her safety. Nick is slightly intimidated but as soon as Sheeni arrives, the pair walks off. It soon becomes clear that Sheeni likes toying with Nick, and at the beach she asks him to lather sunscreen onto her. She notices that he gets an erection and comments on it, joking that “for all he knows [she] could be wet with desire.” As they leave the beach, Nick tries to hold her hand but Sheeni tells him that she has a boyfriend, Trent. She recites some of Trent’s “futuristic” poetry, which Nick openly mocks. Nick walks off dejected.

Nick swings by the next day to apologize, but tries to change his style to seem better than he is. Sheeni tells him that she is going on a hike, but that she would invite him if he had proper provisions. Nick says he likes to do all his hiking free form and tags along. Once they’ve hiked into the woods, Nick needs to pee and while he does, Sheeni reads his journal. Nick gets pissed when he notices it, and she offers her journal for him to read. She comments that his love for her (and thoughts of killing himself over her) was cute. She tells him to kiss her and the pair start to make out.

Nick and Sheeni begin to have make out sessions, which Mrs. Saunders does not approve of. During their first session, Sheeni slips Nick a letter telling them that despite the fact she has a boyfriend, they are young and despite whatever outcome awaits them, they should just have fun. Jerry takes them to buy a rusty old trailer to call their own. While there, Sheeni sees a puppy she wants, so Nick trades a subway card to get the dog, affectionately dubbed Albert by Sheeni. The next day, Jerry throws out his back having sex with Estelle. Nick tells Sheeni that he has to leave and offers to take Albert since he’s “their love child” and the Saunders don’t like dogs. Sheeni tells him that it was fun while it lasted, but Nick proposes a plan to be together: 1.) Get his dad a job in Ukiah since George was just laid off 2.) Be bad enough that Estelle can’t handle him. Sheeni is impressed by his initiative and agrees.

Upon returning home, Nick, Estelle and Jerry see that the lemon car is gone from their lawn. Once they open the door however, they see that the car is in their living room. Jerry is impressed since the Marines broke into the house and reassembled the car piece by piece. Nick calls Sheeni and she tells him that she doesn’t think it will work out. She tells him that she’ll probably move to France and marry a Frenchman named Francois. Nick snaps, and produces a split personality called “Francois Dillinger” (also Michael Cera, with blue eyes, a moustache, tan and French clothing), to represent his bad side, and nail Sheeni.

Jerry goes to the supermarket and has a heart attack. A police Officer, Lance (Ray Liotta), comes and tells Estelle the news of Jerry’s passing. Francois takes over and destroys Estelle’s bras, flushes her jewelry and makes a mess. The next morning, Lance is eating breakfast with Estelle and Francois tells asks why he wasn’t asked before Estelle started having sex with Lance in their house. Estelle apologizes, but Francois attempts to provoke Lance, citing laws against sleeping with people who call for help. Lance tells him to drop it, but Francois asks if he’ll shoot him. Lance gets upset and Estelle calms him down, attempting to mediate. Francois throws his cereal bowl over and walks out of the house.

Sheeni succeeds in getting Nick’s father a job at the local magazine run by Trent’s father. George takes his 20-year-old girlfriend, Lacey (Ari Graynor), up to Ukiah to take the job. Nick realizes that he isn’t working hard enough so Francois takes over and they steal Jerry’s crappy trailer and car. They take it to the middle of town and put some gasoline cans in the trunk. As they are driving up the hill, the trailer latch breaks and crashes into a diner. Then Francois steps out of the car and lets it role back. The car hits the trailer and explodes, causing a 5 million dollar fire. Several witnesses identify Nick as the arsonist. Nick calls Sheeni and tells her that he “burned the town down” for her, something Mrs. Saunders overhears.

When Nick gets home, Lance throws him against the wall, accusing him of setting off the fire. Estelle flips and Lance agrees to cover for Nick assuming that Estelle will keep having sex with him. Lance convinces Estelle to send Nick to George in Ukiah, and then drags Nick upstairs to whip him. Francois takes the beatings and when Lance whips him, Francois asks “you done yet, chief?”

Upon returning to Ukiah, Nick seeks out Sheeni only to find that her parents sent her to an expensive French boarding school to keep her away from Nick. Sheeni leaves Nick a letter saying that it’s a good opportunity for her. George and his girlfriend send Nick to the public school where he befriends Vijay Joshi (Adhir Kalyan), an Indian American. Vijay tells Nick of Trent’s transfer to Sheeni’s school, which infuriates Nick. Nick and Vijay drive to Sheeni’s boarding school after she sends him a letter describing Trent’s attempt to become popular (and her extremely slutty French roommate, to Vijay’s delight).

Upon arriving, Sheeni is happy to see Albert and Nick. She takes them to the soccer field to watch a game while Vijay woos Taggarty (Rooney Mara), the slutty roommate. That night, Taggarty sneaks the boys in by distracting the prefect with her “lady troubles.” The boys set up camp on the floor as Taggarty stares at them, trying to decide who to sleep with. Nick is uncomfortable about it and goes and whispers to Sheeni, requesting to sleep together. She shoots him down since other people are in the room. Nick goes out to the bathroom where he encounters a bulimic girl, Bernice Lynch. He tells her that he is Sheeni’s boyfriend and staying the night and tells her that Trent has been saying terrible things about her behind her back and that all his poetry is plagiarized. He returns to the room and sees Vijay having sex with Taggarty. Francois tells him that he will NOT sleep on the floor so he goes over the Sheeni and asserts himself. She is so impressed that she consents and they begin to fool around when the matron of the dorm enters and screams at the boys, chasing them out of the building.

The duo drive away in nothing but their boxers: Vijay thrilled with losing his virginity and Nick thwarted once again. Their car then breaks down and the two walk toward the nearest payphone a couple of miles away. Nick calls Mr. Ferguson, convincing him that Vijay is an illegal in search of a safe house in Ukiah. Ferguson drives Vijay home and then Nick says that Ferguson could spend the night at his dad and they walk in on George and his girlfriend fighting with each other.

The next day, Nick walks by Sheeni’s house dejectedly and is called out to by her mysterious brother, Paul (Justin Long). Paul and Nick smoke some weed and Nick asks how Paul knew him. He said they were friends in another life and that he knows that Nick “burnt down his hometown” for Sheeni. Nick asks if he was an arsonist in a past life, and Paul tells him that Sheeni was. Nick leaves to run some errands. He writes a letter to Bernice and manipulates her into smearing Trent’s reputation and slipping Sheeni some sleeping pills to get her expelled for her bad grades.

When he returns home, he sees Paul with Lacey and Mr. Ferguson on shrooms. Paul gives Nick the bag and Francois makes him eat them all with a “have a nice trip.” Nick hallucinates the Kama Sutra and when George comes home he sees everyone on shrooms. Paul and George get into a fight over how George treats Lacey, and Lacey leaves with Paul. Paul calls to invite Nick to Thanksgiving dinner at the Saunder’s trailer and tells him that Sheeni was expelled and will be there for dinner.

While preparing for the dinner, Estelle calls to tell Nick that she broke up with Lance. Lance told the police everything and they are coming to arrest Nick. Francois asks if Sheeni is worth going to jail for. Nick dresses for the dinner and goes over. He sees that Paul has drugged his parents and Lacey and Sheeni are there as well. Sheeni tells Nick that she got expelled and that she’s upset that her brother has drugged her parents. Nick asks if she wants to run away with him and tells her that the police are after him. They sit down for dinner and Trent (Jonathan B. Wright) arrives. He reveals that he found a letter from Nick to Bernice, which instructed her to drug Sheeni and smear Trent’s reputation. Trent called the police and tries to intimidate Nick into staying. Sheeni gets extremely upset and Nick is forced to flee upon the arrival of the cops.

He goes home, where George tells him the police came. Nick asks for the car keys, but George instead goes to call the cops. Nick tells him not to and the two start fighting in front of Mr. Ferguson. Mr. Ferguson toss Nick the keys after George starts hitting him, and Nick steals George’s car and drives away. Francois tells Nick that he’s not going to be able to see Sheeni again, and Nick smacks Francois in the head. Francois wakes Nick up the next day and tells him he’s “going to help get the girl.”

Francois calls Lance and tells him that he intends to surrender at the high school. Nick drives the car to the cliff above the lake in front of the school and strips. He leaves his wallet and clothes, takes hi money out of the wallet and puts the car into drive, intent on faking his death. The car lands in the shallow lake, to the amusement of the police. Nick runs away in his boxers. He makes it to town and buys a dress and wig. He goes to Sheeni’s house pretending to be “Carlotta”, a church going classmate of Sheeni. Sheeni knows it’s Nick but lets him in.

Upstairs, the two have a heart to heart and Nick tells Sheeni he loves her. They make up and have sex. Once they’re done, Sheeni asks if Nick’s “him”, meaning the embodiment of everything she wants (Francois). Nick tells him that he’s only Nick and that’s all he’s going to be. Trent arrives and bursts into the room. He and Nick get into a fistfight, which is quickly broken up by a police officer. Nick is placed under arrested and comments, “at least he isn’t going to jail a virgin.” Sheeni tells Nick that he’s going to juvenile detention and will be out in 3 months. The cop puts Nick in his cruiser and Nick reflects on how Sheeni will wait for him and they will be together.

The End

Animated Credit Sequence:
Nick makes it through Juvie (with some help from Francois). Upon release, Sheeni picks him up in a red car with Albert and they drive through Ukiah. Paul and Lacey are living together, Trent is mowing Estelle’s lawn, and Mr. Ferguson is still crashing in George’s house. Lefty has successfully wooed Millie and Vijay is in a fulfilling sexual relationship with Taggarty. Nick and Sheeni travel the world and get their happy ending.